#2 Dean Ambrose cashes in at Money in the Bank 2016
We should've known when Dean Ambrose won the Money in the Bank ladder match that he wasn't going to wait long to make his move. The Lunatic Fringe cashed in on his golden opportunity on the same night he won it.
However, this was more than just a quick cash-in. Dean Ambrose was a member of one of the greatest stables of all time; The Shield. His former stablemates? They were battling for the WWE World Heavyweight Championship in the main event.
The WWE Universe was shocked when Seth Rollins returned from injury at Extreme Rules 2016, attacking then-champion Roman Reigns. At Money in the Bank, the Architect defeated Reigns to reclaim the title he never lost. Unfortunately for him, it didn't last long.
A sheer 33 minutes after capturing the Money in the Bank briefcase, Ambrose cashed in on Rollins to capture his first, and only, WWE Championship. This also served as the only night in the company's history when every member of a stable has held the WWE Title.
#1 Kane cashes in at Money in the Bank 2010
Whew, the Big Red Machine is associated with a lot of great matches and moments, huh? Well, Roman Reigns may have beaten his Royal Rumble record, but it's very doubtful anyone will be able to top this.
At Money in the Bank 2010, Kane won one of two ladder matches. Money in the Bank featured one for SmackDown and one for RAW. After a grueling 26 minutes, he ascended the ladder to win the briefcase. A mere 22:28 later, and Kane made his move on then-World Heavyweight Champion Rey Mysterio.
Kane demolished the Lucha legend, capturing his final world title with WWE after a Chokeslam and a Tombstone Piledriver.